US20230339836A1 - Method for producing reduced coenzyme q10 form ii crystals - Google Patents

Method for producing reduced coenzyme q10 form ii crystals Download PDF

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Publication number
US20230339836A1
US20230339836A1 US17/799,036 US202117799036A US2023339836A1 US 20230339836 A1 US20230339836 A1 US 20230339836A1 US 202117799036 A US202117799036 A US 202117799036A US 2023339836 A1 US2023339836 A1 US 2023339836A1
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Prior art keywords
reduced coenzyme
type crystal
temperature
production method
crystal
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Pending
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US17/799,036
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English (en)
Inventor
Shiro Kitamura
Koichi Kinoshita
Takahiro Ueda
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Kaneka Corp
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Kaneka Corp
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Assigned to KANEKA CORPORATION reassignment KANEKA CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KINOSHITA, KOICHI, KITAMURA, SHIRO, UEDA, TAKAHIRO
Publication of US20230339836A1 publication Critical patent/US20230339836A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
    • C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • Coenzyme Q is an essential component widely distributed in living organisms from bacteria to mammals, and is known as a component of mitochondrial electron transfer system in cells in the living body. Coenzyme Q serves as a transfer component in the electron transfer system by the repetition of oxidation and reduction in mitochondria, and, further, reduced coenzyme Q is known to have antioxidant activity.
  • the major component in humans is coenzyme Q10 which is one having 10 repeating structures in the side chain of coenzyme Q, and usually, about 40% to 90% thereof is present in the living body as the reduced form.
  • the physiological activity of coenzyme Q includes activation of energy production by mitochondrial activation, activation of cardiac function, an effect of stabilizing cell membranes, and an effect of protecting cells by antioxidant activity.
  • the method for producing a reduced coenzyme Q10 Form II-type crystal is characterized by comprising:
  • the mixed solution containing ethanol and reduced coenzyme Q10 is not particularly limited as long as it contains ethanol and reduced coenzyme Q10. It may be a uniform solution in which reduced coenzyme Q10 is dissolved in ethanol or a slurry in which part of reduced coenzyme Q10 is dissolved in ethanol but the other part is not dissolved and is suspended. However, it is preferably a uniform solution in which reduced coenzyme Q10 is dissolved in ethanol.
  • the temperature T p can be appropriately controlled depending on the dissolved concentration C p of the reduced coenzyme Q10 at that time.
  • the temperature T p can be from 5° C. to 43° C.
  • the temperature T p may be a constant temperature.
  • the expression “decrease the temperature T p over time” includes decreasing the temperature T p stepwise or continuously over time.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US17/799,036 2020-02-12 2021-01-29 Method for producing reduced coenzyme q10 form ii crystals Pending US20230339836A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2020-021358 2020-02-12
JP2020021358 2020-02-12
PCT/JP2021/003220 WO2021161807A1 (ja) 2020-02-12 2021-01-29 ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶の製造方法

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US20230339836A1 true US20230339836A1 (en) 2023-10-26

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US (1) US20230339836A1 (https=)
EP (1) EP4105194A4 (https=)
JP (2) JPWO2021161807A1 (https=)
CN (1) CN115087631B (https=)
WO (1) WO2021161807A1 (https=)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022202213A1 (ja) * 2021-03-26 2022-09-29 株式会社カネカ ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶又はその結晶性固体の製造方法
WO2022202214A1 (ja) * 2021-03-26 2022-09-29 株式会社カネカ ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶又はその結晶性固体の製造方法
EP4317125B1 (en) * 2021-03-26 2026-04-29 Kaneka Corporation Method for producing form-ii type reduced coenzyme q10 crystal or crystalline solid of same, and crystallizing apparatus
JPWO2023120553A1 (https=) * 2021-12-24 2023-06-29
JPWO2023120557A1 (https=) * 2021-12-24 2023-06-29
JPWO2024204380A1 (https=) * 2023-03-30 2024-10-03

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7145044B2 (en) * 2001-07-13 2006-12-05 Kaneka Corporation Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
US11453633B2 (en) * 2018-08-30 2022-09-27 Kaneka Corporation Production method for crystal of reduced coenzyme Q10 having excellent stability

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3889481B2 (ja) 1996-08-16 2007-03-07 株式会社カネカ 医薬組成物
TWI237018B (en) 2001-07-13 2005-08-01 Kaneka Corp Method of producing reduced coenzyme Q10 crystals
JP4170657B2 (ja) 2001-07-13 2008-10-22 株式会社カネカ 還元型補酵素ｑ１０の結晶化法
WO2009057611A1 (ja) * 2007-10-30 2009-05-07 Kaneka Corporation 含水有機溶媒を用いる還元型補酵素ｑ１０の製造方法
JP5998135B2 (ja) * 2011-06-24 2016-09-28 株式会社カネカ 安定性に優れた還元型補酵素ｑ１０結晶
JP6704433B2 (ja) 2018-08-02 2020-06-03 三菱電機インフォメーションシステムズ株式会社 入退室管理サーバおよび入退室管理システム

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7145044B2 (en) * 2001-07-13 2006-12-05 Kaneka Corporation Method of producing reduced coenzyme Q10 using solvent with high oxidation-protective effect
US11453633B2 (en) * 2018-08-30 2022-09-27 Kaneka Corporation Production method for crystal of reduced coenzyme Q10 having excellent stability

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Publication number Publication date
CN115087631A (zh) 2022-09-20
CN115087631B (zh) 2024-05-14
EP4105194A4 (en) 2024-03-13
JPWO2021161807A1 (https=) 2021-08-19
EP4105194A1 (en) 2022-12-21
WO2021161807A1 (ja) 2021-08-19
JP2025109930A (ja) 2025-07-25

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